Piperidine → 5-(2-Cyanoethyl) 3-benzyl 4-(3-chlorophenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1700336Notes

Reaction equation

HRID 1700336 reaction equation
[CH3:1][O:2][CH:3]([O:17][CH3:18])[C:4](=O)[CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.N1CCCCC1.[NH2:34]/[C:35](/[CH3:44])=[CH:36]\[C:37]([O:39][CH2:40][CH2:41][C:42]#[N:43])=[O:38]>C1C=CC=CC=1.CC(O)C.O>[Cl:19][C:20]1[CH:21]=[C:22]([CH:23]2[C:36]([C:37]([O:39][CH2:40][CH2:41][C:42]#[N:43])=[O:38])=[C:35]([CH3:44])[NH:34][C:4]([CH:3]([O:17][CH3:18])[O:2][CH3:1])=[C:5]2[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 136714102-Cyanoethyl 3-aminocrotonateHCID 18318278Benzyl 4,4-dimethoxy-3-oxobutyrate

Product 1

HCID 701551985-(2-Cyanoethyl) 3-benzyl 4-(3-chlorophenyl)-2-dimethoxymethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
120 °C

Procedure

3.84 g (7.52 mmol) of benzyl 4,4-dimethoxy-3-oxobutyrate, 1.30 ml (11.5 mmol) of 3-chlorobenzaldehyde and 0.114 ml of piperidine were heated under reflux in 11.5 ml of benzene overnight while water was removed. The reaction solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue thus obtained and 1.77 g (11.5 mmol) of 2-cyanoethyl 3-aminocrotonate were heated at 70° C. under stirring in 57.5 ml of 2-propanol overnight. The reaction mixture was then heated at 120° C. under stirring under atmospheric pressure for 4 hours while 2-propanol was evaporated. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

Workup

  1. customwas removed
  2. washThe reaction solution was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue thus obtained
  6. customwas evaporated
  7. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-b61d2bee8c8f405ebd5a6f871d7d3521
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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